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Dudley Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Dudley vacation rentals

Interior

Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (3 reviews)
"I was looking for a place that was central to a couple of Renaissance Faires in the area and ended uo choosing this one due to its location and affordability. What an awesome place to stay. We're considering staying here next year when the Faires return."
United States
Kevan W.
The price is AED 612
AED 968 total
includes taxes & fees
28 Jun - 29 Jun
Spacious, unique barn with beautiful views.
Exterior

Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (31 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
The price is AED 645
AED 945 total
includes taxes & fees
28 Jun - 29 Jun
Dove Cabin up in the Trees
Interior

The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (37 reviews)
"Such a fun getaway!"
United States
Patrice D.
The price is AED 514
AED 774 total
includes taxes & fees
9 Jul - 10 Jul
The Tree House at Underhill Hollow
Exterior

Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (22 reviews)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
The price is AED 463
AED 690 total
includes taxes & fees
24 Jun - 25 Jun
Wizard's Roost at Underhill Hollow
Interior

Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
The price is AED 253
AED 365 total
includes taxes & fees
24 Jun - 25 Jun
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Terrace/patio

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (40 reviews)
"Very nice area."
United States
maureen p.
The price is AED 551
AED 1,290 total
includes taxes & fees
7 Jul - 8 Jul
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Interior

Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.4 out of 10, Exceptional, (10 reviews)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is AED 551
AED 1,260 total
includes taxes & fees
25 Jun - 26 Jun
Trainmaster's Inn - Caboose
Property grounds

SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (15 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AED 463
AED 690 total
includes taxes & fees
24 Jun - 25 Jun
SteamPunk Bunk House and Intergalactic Way Station
Smart TV

Serenity meets Taradise

Serenity meets Taradise
Union
The price is AED 397
AED 614 total
includes taxes & fees
24 Jun - 25 Jun
Serenity meets Taradise
Interior

Angel Sky Challenge

Angel Sky Challenge
Worcester
2.0 out of 10, (1 review)
"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "
United States
Cameron R.
The price is AED 588
AED 942 total
includes taxes & fees
24 Jun - 25 Jun
Angel Sky Challenge
Exterior

Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (34 reviews)
"The tree house matched the description perfectly! The host was very responsive, the house was clean, and the temperature was comfortable. All instructions were provided prior to our arrival and easy to understand. The manager was friendly and we loved spending time with the animals. It was a little pricey but I would stay again. Great getaway for my husband and i to connect with nature!"
United States
Pattie
The price is AED 579
AED 1,194 total
includes taxes & fees
1 Jul - 2 Jul
Treehouse - Countryside - Farm Animals - Fire Pit
Smart TV

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.6 out of 10, Exceptional, (47 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Bathroom

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.6 out of 10, Exceptional, (32 reviews)
"Lovely and great location "
United States
Kimberlee K.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Property grounds

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.8 out of 10, Exceptional, (16 reviews)
"We loved the ambience, super quiet, my kids love the animals The host was super comunicative making sure we was good during our stay"
United States
Silvino
The price is AED 387
AED 952 total
includes taxes & fees
7 Jul - 8 Jul
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Exterior

Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (1 review)
"Wonderful stay in the cottage. Great location, and prompt and friendly communication from the owner. Beautifully kept vintage home - such a gem!"
United States
K C.
The price is AED 605
AED 695 total
includes taxes & fees
24 Jun - 25 Jun
Cottage by the Castle – Downtown Spencer
Exterior

The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (32 reviews)
"Loved the carriage house and nicely decorated with all the artwork! I wish we could have stayed longer. If I need a place to stay in the area, I will definitely be staying there!"
United States
Patti G.
The price is AED 422
AED 774 total
includes taxes & fees
22 Jul - 23 Jul
The Carriage House at Chaprae Hall
Property grounds

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
9.2 out of 10, Wonderful, (5 reviews)
"This is a nice place for solo travelers or a small family with kids. The kid’s bedroom has tons of games and is themed nicely. The backyard is huge but unfenced and the property is off of a busy road. Th house itself was clean and the host offered a variety of things such as slippers for the whole family, house shoes, and bath things for everyone. The house does not have a tv but the wifi works well. "
United States
Chantay-Rose
The price is AED 716
AED 894 total
includes taxes & fees
29 Jun - 30 Jun
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Private kitchen

Close to Colleges: Worcester Apt w/ Lake Access!

Close to Colleges: Worcester Apt w/ Lake Access!
Worcester
10.0 out of 10, Exceptional, (15 reviews)
"The amenities were great."
United States
Missie B.
Close to Colleges: Worcester Apt w/ Lake Access!
TV

6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is AED 624
AED 2,430 total
includes taxes & fees
24 Jun - 25 Jun
6 Beds Home w/Game Room Perfect for Groups
House (2 Bedrooms) | Front of property

Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!
3.0 star property
Worcester
The price is AED 720
AED 1,660 total
includes taxes & fees
19 Jul - 20 Jul
Lakefront Cottage 2 Mi to Palladium in Worcester!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Dudley Hotel Reviews

Scottish Inn Sturbridge

Scottish Inn Sturbridge

10/10 Excellent
"The town of Sturbridge is a perfect setting for a little break away from the hustle and bustle of city life. Rooms clean, although dated. Location good and parking in abundance."
Lee Andrew 3-night trip
Posted 2 hours ago
Scottish Inn Sturbridge

Frequently asked questions

Are there vacation rentals in Dudley?

Yes, there are vacation rentals in Dudley near TriState Speedway, or you can go with a secluded option if you want a relaxing stay. Dudley is known for its restaurants.

What's the top vacation rental that Dudley has to offer?

3-bedroom house on Webster Lake with amazing views, beach and boat launch access: You might want to consider this vacation home rental near Dudley, which is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Dudley?

Choose from 3 Expedia vacation rentals in Dudley for a memorable vacation.

What’s there to see and do in Dudley?

Stevens Park and Berthol Field are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include TriState Speedway. Dudley Hill Golf Club at Nichols College and Conant Library are other places to visit while you're in town.

What’s a vacation rental in Dudley like?

Vacation rentals are private properties you can book for a long or short time in Dudley. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family gatherings.